3-Fluorophenol → HCID 57968647, compound

HRID 882757Notes

Reaction equation

HRID 882757 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([O:13][C:14]([N:16]1[CH2:20][C@H:19](O)[CH2:18][C@H:17]1[C:22]([N:24]1[CH2:30][CH2:29][CH2:28][N:27]([CH:31]2[CH2:34][CH2:33][CH2:32]2)[CH2:26][CH2:25]1)=[O:23])=[O:15])([CH3:12])([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:9]([O:13][C:14]([N:16]1[CH2:20][CH:19]([O:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH2:18][C@H:17]1[C:22]([N:24]1[CH2:30][CH2:29][CH2:28][N:27]([CH:31]2[CH2:32][CH2:33][CH2:34]2)[CH2:26][CH2:25]1)=[O:23])=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 97433-FluorophenolHCID 11776TriphenylphosphineHCID 44600522HCID 44600522, compound

Product 1

HCID 57968647HCID 57968647, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of 3-fluorophenol and (2S,4R)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester was performed as described in Example 11, using resin bound triphenylphosphine and CH2Cl2 to give the title compound as a mixture of diastereomers (89:11), as determined by chiral SFC. MS (ESI): mass calcd. for C25H36FN3O4, 461.27; m/z found, 462.3 [M+H]+. 1H NMR (CDCl3): 7.25-7.16 (m, 1H), 6.69-6.53 (m, 3H), 5.01-4.69 (m, 2H), 3.89-3.42 (m, 6H), 2.92-2.79 (m, 1H), 2.69-2.20 (m, 6H), 2.06-1.72 (m, 6H), 1.71-1.53 (m, 2H), 1.44-1.39 (m, 9H).

Sources & evidence

ORD record
ord-cd5973ed57f44830a8c4fa03040e1917
Source dataset
uspto-grants-2012_08
Patent number
US08236792B2

Reaction notes

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